Manufacture of condensation products



Patented Deci. 31, 192 9 I UNITED STATES "PATENT. OFFICE furor-nanMICHEL, or nnanmenn, mnnnannnrm' GERMANY, Assrenon 'ro r. e.

FARBENINDUSTRIE' AKTIENGESELLSCHAIT, OF FRANKFORT-ON-THE-MAIN, GER-MANY, A CORP ORATION OF GERMANY muurno'ronn or CONDENSATION rnonucrs-The invention relates to new condensation 'roducts from olefines" andpolynuclear hydrocarbon compounds 3 and to a process of making the same.

5 As I have setforth in my U. S. Patent No. 1,667 ,214, issued April24th, 1928 homologues or condensation product'sof naphthalene hy-'drocarbon. compounds are obtained by react- I,

ing with olefines upon naphthalene hydrocarbon compounds underconditions of elevated temperature and super-atmospheric pressure.

Thepresent-1nvention represents a further developmentand in accordancetherewith I have found that also other polynuclear hydrocarbon compoundsthan naphthalene hydrocarbon compounds, namely polynuclear hydrocarboncompounds having at least three nuclei such as for example acenaphthene,fluorene, phenanthrene, and the derivativesthereof. inasmuch as theycontain atleast one double linkage in a nucleus (the aromatic nucleusbeing considered as containing three double linkages) readily react withol'efines in the presence ofcatalytically acting substances to formalkyl derivatives or higher condensation products.

Among the catalytically acting substances which have been foundeffective in uniting olefines with the said polynuclear hydrocarboncompounds are metallic halides particularly. aluminum chloride and ironchloride, and addition compounds of, say, aluminum mixtures containingolefines such as for ex ample the gaseous mixtures resulting from thanethylene.

having at least three nuclei it is not necessary cracking operations,oil gas, and the like. The polynuclearcompounds, too, need not'be intvpure state; crude materials and technical mixtures as are obtained in;distillingcoal 'tar or from the mother liquors-of the refining Drawing.Application filed December 3,' 1928, Serial No. 323,574, and in GermanyDecember 8, 1927.

of. crude anthracenehave proved quite suitsuch as cyclohexene willmore-readily react Y ready takes place at atmospheric pressure'butadvantageously it is accelerated by application pf superatmosphericpressure; The

tem ierature of reaction is found to lie'above 50 C. and in particularbetween 100 and 200 C. the most favorable results are obtained.

The resulting products are alkylatedderivjatives of the polynuclearcompounds or, by

more intensified action, higher condensation products thereof. Accordingto the relative proportions of the olefine and polynuclear In some casesreaction alcompounds one or more moles of olefine com- W bine with thepolynuclear compound to form .oily or crystalline alkylated. derivativesor highercondensation products of oily or resinous nature. Those alkylderivatives wherein some of the alkyl groups contain more-than onecarbon atom, as well as all the higher conj densation products have notbeen hitherto known. I

The invention is illustrated by the follow- Parts are by w i ht Ihalides and olefines, with either f thesgfl I be combined also otheig-z- EwampZe 1 andBO parts of anhydrousaluminum chloride are stirredfor some 2 hours with propylene In an autoclave 500 parts ofphenzinthrene ing examples but not restricted thereto.- The gas under a:pressure ofabout 15 atmospheres H and at a temperature of from to C; Anincrease in weight of270 parts is attained' lj After cooling andwashingwith-water, the reaction product is distilled under 1 mm.

There are ob- 1 tained the following oily fractions increasing pressure(mercury gauge).

in viscosity wi ththe boiling point:

(1') 40 parts ofa light' yellow oil boiling from to 200C. (2) 350 parts"of a yellow oil boiling from. J 200 to 210 C. 2

boiling from210'to 215 C.

Example Q 450 parts of acenaphthene and 45 partsi'of I anhydrousaluminum chloride are stirred halide.

with propylene gas under a pressure of'about 12 atmospheres and at atemperature'of from 100 to 120 C. As soon as reaction has begun, furtherheatingis not necessary since the temperature is maintained due to thereaction heat generated. After 310 parts of propylene have beenabsorbed, no further reaction takes place. The liquid reaction productis washed with water and by distilling it under 1 mm. pressure (mercurygauge) separated into an oily fraction boiling from 150 to 200 C. and asecond fraction boiling from 200 to 210 C. which solidifies after sometime to a crystalline mass.

and 50 parts of anhydrous aluminum chloride. are stirred with propylenegas under a pres-' sure of about 20 atmospheres and at a temperature ofabout 120 (1, until an increase in The fractions (2) and (3) areexcellent lu-i halide.

I11 testimon my hand;

Weight of 200 parts is attained. After washin with water'a soft resinousbody remains.

n the following claims the generic term polynuclear hydrocarbon compoundis used to denote a polynuclear aromatic hydrocarbon, its homologues andhalogenated and/or. partially hydrogenated derivatives thereof.

I claim:

1. Process which comprises reacting with an olefine upon a polynuclearhydrocarbon compound having at least three nuclei in'the presence of acatalytically actingmetallic 2. Process which comprises reacting with anolefine upon a polyn'uclear hydrocarbon compound having at least threenuclei in the presence of a oatalytically "actin I metallic halide underconditionsof elevate temperature over 50 'C. and superatmospheric pressure chloride, under superatmospheric ressure and at a temperature'ofabout 100 4. Process which comprises reacting with propylene uponphenanthrene inithe presence of aluminum chloride under a pressure offrom 10 to 20 atmospheres and at a temperature of from-about 100 to 150C.

5. Process which comprises reacting with an olefinic-gasupon apolynuclear hydrocarbon compound having atleast three nuclei in 3.Process which comprises reacting with, an olefine upon a polynucleararomatic hy- (3) 90 parts of a yellow highly viscous oil the presence ofa catalytically acting metallic RICHARD MICHEE.

